Upperville Ski Chalets Rentals & Holiday Homes

There are a lot of options in Upperville. If you plan on staying in the Upperville area, consider making a reservation for a few nights at one of these properties as these have been rated the top Ski Chalet Rentals in Upperville:

• The Mill House in Upperville -
• Stylishly restored 1800's historic home- heart of Virginia hunt & wine country!
• 18th Century Stone Cottage minutes from historic Middleburg
• Lovely Guest House 2.5 miles from downtown Middleburg
• Historic house in Upperville! Wineries, equestrian events, great location!
• Hunt Country cottage in Upperville!
• Peaceful Mountain Retreat Near Appalachian Trail, Wineries, Breweries and More
• Cozy Country Getaway in the Heart of Upperville
• Renovated 1880s farmhouse near the Blue Ridge and Sky Meadows with amazing views
• Charming 3-bedroom cottage located on historic Seaton Place Farm in Delaplane VA

There are many ski chalets available in Upperville; however, here are the most popular ski chalets listed in Upperville:

• Mountain View + Hot tub + Sauna + Yoga + Trails + Wineries + Geodesic stargazing dome
• Stylishly restored 1800's historic home- heart of Virginia hunt & wine country!
• Historical Paris Cabin on Farm with Fire Pit!
• Grand 9BR Provenance Manor Ideal for Gatherings
• 18th Century Stone Cottage minutes from historic Middleburg

Womenintravel offers availability throughout the year, but you can book pre-Christmas, mid-January, or before and after the school break at Easter are the best times for renting in Upperville.

At Womenintravel most of our ski chalets are perfect for families. Check out the complete list of ski chalets in Upperville to find what works for you.

Yes, there are plenty self-catering family ski chalet in Upperville that have hot tubs & other amenities.